EP2976420B1 - Neuartige mittel und verwendungen und verfahren zur herstellung davon - Google Patents

Neuartige mittel und verwendungen und verfahren zur herstellung davon Download PDF

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EP2976420B1
EP2976420B1 EP14724125.1A EP14724125A EP2976420B1 EP 2976420 B1 EP2976420 B1 EP 2976420B1 EP 14724125 A EP14724125 A EP 14724125A EP 2976420 B1 EP2976420 B1 EP 2976420B1
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hops
water
extraction
solvent
extract
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French (fr)
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EP2976420A1 (de
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David Cook
Robert LINFORTH
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Barth-Haas Uk Ltd
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Barth-Haas Uk Ltd
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    • C—CHEMISTRY; METALLURGY
    • C12—BIOCHEMISTRY; BEER; SPIRITS; WINE; VINEGAR; MICROBIOLOGY; ENZYMOLOGY; MUTATION OR GENETIC ENGINEERING
    • C12H—PASTEURISATION, STERILISATION, PRESERVATION, PURIFICATION, CLARIFICATION OR AGEING OF ALCOHOLIC BEVERAGES; METHODS FOR ALTERING THE ALCOHOL CONTENT OF FERMENTED SOLUTIONS OR ALCOHOLIC BEVERAGES
    • C12H1/00—Pasteurisation, sterilisation, preservation, purification, clarification, or ageing of alcoholic beverages
    • C12H1/02—Pasteurisation, sterilisation, preservation, purification, clarification, or ageing of alcoholic beverages combined with removal of precipitate or added materials, e.g. adsorption material
    • C—CHEMISTRY; METALLURGY
    • C12—BIOCHEMISTRY; BEER; SPIRITS; WINE; VINEGAR; MICROBIOLOGY; ENZYMOLOGY; MUTATION OR GENETIC ENGINEERING
    • C12C—BEER; PREPARATION OF BEER BY FERMENTATION; PREPARATION OF MALT FOR MAKING BEER; PREPARATION OF HOPS FOR MAKING BEER
    • C12C3/00—Treatment of hops
    • C12C3/04—Conserving; Storing; Packing
    • C12C3/08—Solvent extracts from hops

Definitions

  • the present invention relates to agents and methods for fining beverages, and in particular for flocculating yeast, or the removal of chill haze, or both. We describe methods for the preparation of such agents
  • the problem is particularly relevant to the brewing and wine manufacturing industries.
  • brewed beverages several ingredients can result in a turbid product which is unacceptable to consumers.
  • Proteins, polyphenols and suspended yeast can all result in a hazed product, and the aim of the fining process is to remove enough of those ingredients to provide a clear product.
  • Isinglass A commonly used yeast flocculating agent in the brewing industry is isinglass.
  • Isinglass is a collagen product obtained from the swim bladder of fish.
  • isinglass is an effective fining agent and yeast flocculating agent, its origin is a matter of some controversy amongst consumers, who may find the use of fish swim bladders distasteful. Vegetarian and vegan consumers do not consider products containing isinglass suitable for their dietary requirements. The question of whether the use of isinglass can render an otherwise kosher product non-kosher is also a debatable point.
  • isinglass therefore limits the acceptability of products and an alternative fining agent, preferably which is able to flocculate yeast, that is economical and easy to produce, and which overcomes these and other disadvantages of the prior art available fining and flocculating agents is required.
  • ITO Memoirs of the College of Science, University of Kyoto, Series A, Vol XXXI, No 2, Article 6, 1967 [XP003022714 ] discloses yeast flocculating effects of hop tannins and malt tannins.
  • US 2009/0169691 describes enhancement of the flocculating effect of pectin by ethanol and CO 2 extracts of hops, through to be attributable isohumulones in the extracts.
  • the present invention provides the use as a fining agent or yeast flocculating preparation of an extract of hops wherein the extract is prepared by a step of extracting hops with a mixed solvent of an organic solvent and water; and a step of solvent removal after the extraction.
  • the fining agent may display yeast flocculating activity.
  • the invention provides a fining agent that does not require the use of fish swim bladders for its production.
  • the agent is produced from hops and is, surprisingly, therefore readily derivable from the brewing process itself.
  • the agent therefore has the advantage of enhanced acceptability since it may be seen as a natural ingredient in products requiring fining.
  • the disclosure further provides methods of providing the fining agent, and uses of the fining agent for flocculating yeast and removing haze from a beverage. Methods of fining, including flocculating yeast, are also described.
  • the hops are whole hops, solvent-extracted hops, or spent hops from a brewing process.
  • the hops used are previously extracted hops. These may have been extracted using a solvent, such as an alcohol, or using CO 2 . These previously extracted hops are therefore a waste product derived from the preparation of hop extracts for brewing purposes, these hops may be referred to as spent hops.
  • hop cones are used for the extraction. Any of the known varieties of hops used in the brewing industry may be used.
  • the organic solvent is present in the mixed solvent in an amount of about 10% v/v or more, preferably 20% v/v or more, more preferably 30% v/v or more.
  • the organic solvent is present in the mixed solvent in an amount of about 90% v/v or less.
  • the organic solvent comprises acetone or alcohol.
  • the solvent is a mixed solvent comprising acetone and water in an amount of 30-90% v/v acetone, preferably 40-80% v/v acetone, more preferably about 70% v/v; or a mixed solvent comprising alcohol and water in an amount of 10-90%> v/v alcohol, preferably 20-90% v/v alcohol, more preferably about 80% v/v.
  • the alcohol is methanol or ethanol or a mixture thereof.
  • the extraction is carried out at a temperature of about 100°C or below, preferably at about 50°C or below, more preferably at about 30°C or below, even more preferably at about 10°C or below.
  • the preparation which may be provided simply by stirring hops in the extraction medium to provide a crude extract, contains the fining agent, which may display yeast flocculating activity.
  • the crude extract is further purified or cleaned up using various known extraction methods, including, but not limited to, solid phase extraction (SPE), liquid-liquid extraction, column chromatography, filtration, ultrafiltration, centrifugation, pH adjustment or enzyme treatment.
  • SPE solid phase extraction
  • liquid-liquid extraction column chromatography
  • filtration filtration
  • ultrafiltration ultrafiltration
  • centrifugation pH adjustment or enzyme treatment.
  • the extraction process may involve stirring hops, and may further include grinding hops in the chosen extraction medium.
  • extraction may be achieved by pumping solvent at various pressures through an extraction cell loaded with hop material.
  • the preparation may be obtained by further purifying the extract by extraction against various solvents.
  • the preparation is purified by extraction with ethyl acetate.
  • the hops are pre-extracted with a solvent such as hexane prior to the extraction with the mixed solvent.
  • the methods may be supplemented by further purification of the fining agent containing preparation, which may display yeast flocculating activity, on one or more solid phase extraction column.
  • the preparation can be loaded into one or more of a cyano column, a Sep-Pak C18 column or a Sephadex LH-20 column.
  • the fining agent containing preparation may be eluted from the cyano column in, for example, 30% acetonitrile, or from the Sep-Pak C18 column with methanol, or from LH-20 with acetone/water mixtures.
  • the invention further provides the use of the preparations of the invention for the fining of samples, and in particular the flocculation of yeast, in need thereof.
  • the preparations will be used in the manufacture of brewed beverages to provide clarified products.
  • the preparation may be used alone in such methods or together with any other known fining agent or flocculating agent, for example, but not limited to isinglass, Irish Moss, PVPP and carrageenan.
  • the invention further provides the use of a proanthocyanidin as a fining agent or yeast flocculent, wherein the proanthocyanidin has a molecular weight of 10 to 150 kDa.
  • a preparation extracted from hops preferably extracted from CO 2 extracted hops, and therefore a waste product of the brewing industry, has potent fining activity, and in particular yeast flocculating activity, and may be used as a fining agent in the preparation of, inter alia brewed beverages.
  • hops may be used as the starting material for the production of the preparations of the invention.
  • Hop cones; powdered or pelleted hops or processed hops; spent hop materials or solvent-extracted spent hop material may be used as sources of the fining material.
  • the fining activity which may include yeast flocculating activity, present in the hops may be extracted very simply and economically by the preparation of a crude extract in water. Alternatively an alcohol or organic solvent based extraction medium may be used. Stirring of hops overnight at room temperature in water provides an extraction medium/preparation with fining activity, which includes yeast flocculating activity.
  • the active agent passes through a 1.2 ⁇ m filter and may be further purified or cleaned up by a variety of known extraction techniques.
  • Extraction may be carried out over a period of minutes or hours, for example 0.5 hours, 2 hours, 3 hours, or more and may be carried out overnight, or for up to 24 hours or for longer. Longer extraction times, for example 24 hours or more, do not diminish the activity of the extracts.
  • the extraction is carried out cold, 0°C or just above. In other embodiments the extraction is carried out at or around at room temperature. In other embodiments the extraction is carried out at an elevated temperature, for example at 30, 40, 50 or 60 °C or higher.
  • Yeast flocculating activity in the extract can be determined and tracked through the purification, or clean-up process simply, in accordance with Example 2, by measuring the OD of a sample containing suspended yeast.
  • the size of the sediment formed may also be used to determine flocculating activity.
  • Flocculation may also be visualised by microscopy as shown in Example 6.
  • the ability of the extracted agent (hop liquor) to reduce haze in a liquid may be determined by measuring the forward scattering from a liquid at an angle of 90°. The higher the scatter the greater the amount of small particles, typically proteins, and thus haze in the liquid.
  • the yeast flocculating activity is extracted in an aqueous mixture of water and an alcohol, such as ethanol or methanol.
  • the activity is extracted from hops in a 10% to 90% (v/v) methanol in water medium.
  • the activity is extracted from hops in a 10% to 90%, preferably about 80%, (v/v) ethanol in water medium.
  • the hops are subjected to extraction with aqueous acetone, and the acetone extract contains the fining agent, which preferably displays yeast flocculating activity.
  • Acetone is preferably mixed with water to provide a solution of acetone at about 50 to about 80% v/v.
  • the extraction medium is about 70% acetone.
  • hop powder is extracted for two hours at ambient temperature in 70% acetone. The sample is filtered, and the acetone removed by rotary evaporation. The sample is adjusted to pH 3.6 and partitioned against 2 volumes of ethyl acetate. The aqueous phase is retained. Following further rotary evaporation to remove ethyl acetate the sample is left to precipitate, and the supernatant contains the active agent. Contaminating species remain in the precipitate.
  • solid phase extraction may be employed.
  • the preparation may be loaded on to C18 SPE cartridges equilibrated with methanol and then water.
  • the sample may be loaded in water and the activity is retained in the cartridge and can be eluted with methanol.
  • an extract prepared from hops by any of the methods described herein may be applied to a cyano column, for example a CN 500/3mL cartridge, preconditioned with acetonitrile (ACN) and equilibrated with water.
  • the sample is loaded in water and may be eluted with 20% or 30% ACN.
  • the ACN elution may be employed as a gradient elution against acetic acid, or may be an isocratic elution.
  • the sample is loaded onto the cartridge in acidic conditions, for example at about pH 3.5.
  • an extract prepared from hops by any of the methods described herein may be applied to an LH-20 Sephadex column in an 80% v/v solution of ethanol.
  • the active agent is eluted with 50% acetone.
  • extracts prepared from hops by any of the methods described herein may be further cleaned up by extraction against organic solvents, column chromatography, filtration, ultrafiltration, centrifugation, pH adjustment or enzyme treatment.
  • the extract may be extracted further against ethyl acetate to remove contaminating products.
  • the preparations of the current disclosure are preferably fining agents that are able to flocculate yeast and clarify brewed beverages. It is thought that the principal active agent of the preparations may be a proanthocyanidin because of its behaviour in the various extraction methods described and exemplified herein, and in view of its characterisation detailed in Example 12.
  • Proanthocyanidins also known as condensed tannins are polymeric flavonoids. Details of their chemistry and methods for their isolation and handling can be found at http: // www.users.muohio.edu / HAGERMAE / .
  • LC-MS analysis of extracts of the invention hydrolysed with butanol/HCL reveals a mass spectrometric profile consistent with the presence of cyanidin and robinetinidin, and the measured visible spectrum of the hydrolysate in butanol/HCl is also characteristic of cyanidin.
  • the LC-MS work confirms this and gives the suggestion that it is catechin and/or epicatechin based. Size fractionation suggests that the proanthocyanidins in the preparations of the invention are in a range from 15 to 50 kDa, but could be larger, e.g. up to 150 kDa.
  • the active ingredient of the preparations is soluble in acetone, and in water at acidic to alkaline pH.
  • the preparations are used for the clarification of brewed beverages by the flocculation of yeast therein. In other embodiments, the preparations are used for the clarification of brewed beverages by the removal of peptides which have precipitated therein.
  • the preparation can be added to beers without a change in the nature of the beer product (other than the clarification). The product, when added to beer has minimal impact on the taste and aroma of the finished beverage.
  • the preparations can be used alone to clarify brewed beverages or can be used together with one or more known fining agents.
  • the preparation of the invention is used together with isinglass to clarify beer.
  • the preparation is used together with carrageenan to clarify beer
  • the preparation is used together with Irish Moss to clarify beer.
  • Other fining agents and combinations of fining agents that may be used together with the preparations of the invention will be apparent to the skilled person.
  • the preparation may be supplied in powdered form following concentration and evaporation of an extract prepared according to any of the methods described herein, using a range of evaporative techniques which will be well known to those skilled in the art.
  • the preparation may be compacted or formed into a tablet.
  • the product may be supplied as a solution in water, ethanol, a water/ethanol mix, acetone or an acetone/water mix, or in a carrier suitable for use in the food and beverage industry, such as propylene glycol.
  • Example 2 2mL of the liquor (or of a water control) from the extraction of Example 1 was added to 12.4mL of 3 day old green beer - near the end of the main fermentation. The sample was mixed for 15 minutes. The tube caps were removed and the samples left to stand for different amounts of time. The OD of 100 ⁇ L of the mixture (removed with a syringe) from 15mm below the meniscus was measured at 600nm after a 10-fold dilution in water. Table 1: OD values for control and hop liquor samples time control 1 control 2 hop 1 hop 2 10 0.79 0.83 0.51 0.33 20 0.85 0.88 0.45 0.35 30 0.84 0.89 0.37 0.40 45 0.92 0.84 0.34 0.33 60 0.80 0.76 0.41 0.39
  • Example 2 A sample of the hop liquor from Example 1 (8mL) was passed through 2 conditioned and equilibrated (4 mL methanol, then 4 mL water) C18 Strata-x cartridges 200mg/6mL (Phenomenex) in series. This "load” was checked for activity (Table 2). Table 2 OD readings for SPE load and water controls Replicate Control water C18 SPE load 1 0.81 0.78 2 0.74 0.73 3 0.76 0.82 The optical readings were performed as described in Example 2 with the samples allowed to stand for 15min before OD measurements were made.
  • the active was retained by the SPE cartridge when loaded in water. Following this attempts were made to recover the active material. In a separate experiment, recovery of the sample from the SPE cartridge was attempted with methanol. A 4mL sample was applied in water, the cartridge was washed with 4mL water and elution was attempted with 4mL methanol. No activity was found in either the wash or elution fractions.
  • the active compound was eluted in the methanol fraction. This behaviour is consistent with that of polymeric proanthocyanidins with a high number of sub-units (reference: Methods in polyphenol analysis. Edited by Celestino Santos-Buelga, Gary Williamson. Royal Society of Chemistry 2003 ).
  • the active eluted in the 20% acetonitrile fraction.
  • Figure 1 shows a plot of the OD vs. amount of hop liquor added. It can be seen that samples containing 2 mL or 1mL appear to have been flocculated, whilst lower amounts gave weaker responses. This shows that for a wholly aqueous extract around 12.5g of hops would have to be extracted to induce yeast flocculation in 4.5 litres of green beer.
  • Figure 2 shows a visual inspection of yeast samples treated with the flocculent preparation (hop liquor) of Example 1 or control (water).
  • Example 1 The extraction of Example 1 was varied to show the effect of temperature, grinding and the addition of methanol to the extraction medium.
  • the extraction was carried out in static incubators for 4.5 hours. 5g of hops were extracted in 150 mL solvent. Grinding was carried out in solvent using an ultra-turrax high shear mixer at high speed for 2 min. For the methanol water mixture the ratio of methanol:water was 50:50.
  • the flocculent therefore appears to be active at a range of molecular weights including both the 3-30 kDa and >30 kDa ranges.
  • Table 9 Depth of sediment (mm) of yeast settling after treatment of 4 different yeasts with a Saaz hop extract yeast Saaz Rep 1 Saaz Rep 2 Water Rep 1 Water Rep 2 Lager Brewing yeast 1 7 6 1 1 Lager Brewing yeast 2 7 8 0 0 YBB (home brew kit 1) 10 10 0 0 YTB (home brew kit 2) 10 10 0 0
  • Figure 7 (a) shows the visible spectrum of a sample (Example 11) hydrolysed in butanol HCl for 20min at 100°C. A maximum was observed at 552nm and the shoulder was at 542nm. These features are consistent with the production of anthocyanidins.
  • Figure 7 (b) shows, for comparison, part of the absorption spectra for a variety of anthocyanidins, and is taken from http://www.ncbi.nlm.nih.gov/pmc/articles/PMC2852856/.
  • the formation of a haze tends to occur when beverages are cooled prior to consumption and is often referred to as a "chill haze”. Whilst the product is unaffected in terms of taste, the appearance can be unappealing to the consumer.
  • An extract preparation/hop liquor according to the invention can be used to reduce or prevent haze formation.
  • Tables 11 and 12 demonstrate that a hop preparation obtained by aqueous alcohol or water extraction (Table 11) or by aqueous acetone or aqueous alcohol extraction (Table 12) of spent hops after solvent extraction is able to reduce the chill haze in beer samples (note that the data in Tables 11 and 12 relate to the fining of different batches of hazy beer).
  • Table 11 Impact of hop preparations obtained from spent Galena hops following supercritical CO 2 extraction, and a commercial isinglass, on chill haze in beer Fining Agent Dosage Rate (mL extract / 0.2 L beer) Haze @ 4°C (H 4°C ) (in EBC Units) Haze @ RT (H RT ) (in EBC Units) Chill Haze (H 4°C -H RT ) (in EBC Units) Unfined Control - 0.83 0.37 0.46 Isinglass (Murphy's Alkleer A) 0.5 0.35 0.33 0.02 Spent Galena hops extracted into 20% ethanol (aq) 4.5 0.5 0.4 0.1 Spent Galena hops extracted into water 3 0.61 0.4 0.21
  • Table 12 Impact of hop preparations obtained from spent hops after CO 2 extraction, and a commercial isinglass, on chill haze in beer Fining Agent Optimal Dosage (mL extract / 0.2 L beer) Haze @ 4°C (H
  • Example 14 Flocculating activity extracted from whole hop cones of various varieties (Reference)
  • Example 15 Aqueous extraction of hops at a range of pH values (Reference)
  • Hops were added to water and the pH of the water/hop slurry was adjusted to a range of pH values using hydrochloric acid or sodium hydroxide. Hop liquor was assayed for flocculation activity based on the amount of extract that was necessary to induce yeast flocculation. As can be seen in Table 14 all of the extracts showed flocculation activity, although this activity was lower at pH 9 than at other pH levels. A lower activity score, indicates less extract was needed to induce flocculation. The optical properties of the extracts were also determined and the extract carried out at pH 3 showed the greatest light transmission indicative of greater clarity. This showed that the extraction of the fining agent can be carried out at a range of pH values. Table 14 Extraction pH Activity Score % Transmission (600 nm) 9 8 58.3 8 4 67.3 7 4 66.3 6 4 65.1 5 4 65.1 4 85.5 3 4 89.3 2 4 63.3

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Claims (12)

  1. Verwendung eines Hopfenextrakts als Klärmittel oder Hefe-Flockungszubereitung, wobei der Extrakt durch einen Schritt einer Extraktion von Hopfen mit einem gemischten Lösungsmittel aus einem organischen Lösungsmittel und Wasser und einen Schritt einer Lösungsmittelentfernung nach der Extraktion zubereitet wird.
  2. Verwendung nach Anspruch 1, wobei das organische Lösungsmittel in dem gemischten Lösungsmittel in einer Menge von ungefähr 10 % Vol./Vol. oder mehr, vorzugsweise 20 % Vol./Vol. oder mehr, bevorzugter 30 % Vol./Vol. oder mehr, vorhanden ist.
  3. Verwendung nach Anspruch 1 oder Anspruch 2, wobei das organische Lösungsmittel in dem gemischten Lösungsmittel in einer Menge von ungefähr 90 % Vol./Vol. oder weniger vorhanden ist.
  4. Verwendung nach einem vorherigen Anspruch, wobei das organische Lösungsmittel Aceton oder Alkohol umfasst.
  5. Verwendung nach Anspruch 1, wobei das Lösungsmittel ein gemischtes Lösungsmittel ist, das Aceton und Wasser in einer Menge von 30-90 % Vol./Vol. Aceton, vorzugsweise 40-80 % Vol./Vol. Aceton, bevorzugter ungefähr 70 % Vol./Vol., umfasst.
  6. Verwendung nach Anspruch 5, wobei der Schritt einer Lösungsmittelentfernung eine Entfernung von Aceton umfasst.
  7. Verwendung nach Anspruch 1, wobei das Lösungsmittel ein gemischtes Lösungsmittel ist, das Alkohol und Wasser in einer Menge von 10-90 %> Vol./Vol. Alkohol, vorzugsweise 20-90 % Vol./Vol. Alkohol, bevorzugter ungefähr 80 % Vol./Vol. umfasst.
  8. Verwendung nach Anspruch 4 oder Anspruch 7, wobei der Alkohol Methanol oder Ethanol oder ein Gemisch davon ist.
  9. Verwendung nach einem vorherigen Anspruch, wobei die Extraktion bei einer Temperatur von ungefähr 100 °C oder darunter, vorzugsweise bei ungefähr 50 °C oder darunter, bevorzugter bei ungefähr 30 °C oder darunter, noch bevorzugter bei ungefähr 10 °C oder darunter durchgeführt wird.
  10. Verwendung nach einem vorherigen Anspruch, wobei der Hopfen ganzer Hopfen, lösungsmittelextrahierter Hopfen oder verbrauchter Hopfen aus einem Brauprozess ist.
  11. Verwendung eines Proanthocyanidins als Klärmittel oder Hefe-Flockungsmittel, wobei das Proanthocyanidin ein Molekulargewicht von 10 kDa bis 150 kDa aufweist.
  12. Verwendung nach einem der Ansprüche 1 bis 11 bei der Herstellung eines Lebensmittels oder Getränks, vorzugsweise wobei das Getränk ein Bier, helles Bier, obergäriges Bier oder Wein ist.
EP14724125.1A 2013-03-22 2014-03-21 Neuartige mittel und verwendungen und verfahren zur herstellung davon Active EP2976420B1 (de)

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GBGB1305297.2A GB201305297D0 (en) 2013-03-22 2013-03-22 Novel agents and uses thereof
PCT/GB2014/050886 WO2014147411A1 (en) 2013-03-22 2014-03-21 Novel agents and uses and methods for the preparation thereof

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AU (1) AU2014234017B2 (de)
CA (1) CA2907820A1 (de)
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AU2022275299A1 (en) 2021-05-10 2023-12-21 Kerry Group Services International Limited Natural fining agent for beverages
GB2608607A (en) * 2021-07-05 2023-01-11 Jose Torrealba Victoria Hop essential compounds extraction and separation unit

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US8697169B2 (en) * 2004-09-20 2014-04-15 Carlton And United Beverages Limited Methods and compositions for fining beverages

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GB201305297D0 (en) 2013-05-01
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AU2014234017B2 (en) 2018-07-26
AU2014234017A1 (en) 2015-10-22
WO2014147411A1 (en) 2014-09-25
EP2976420A1 (de) 2016-01-27
US20160053212A1 (en) 2016-02-25

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